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Synthesis Help: Adding part to terminal alkyene

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Meter:


Hi all.

I'm a little stumped as to what reagents I need for this step. It's entirely possible that several different reactions are required.

My initial thought was to do some type of "alkylation" to the terminal alkyne using NaNH2 with an appropriate compound, but it seems that those only work for haloalkanes? Anyway I would need a way to add the hydroxyl group as well. Can I get a hint? 

Meter:
I think I figured it out.

Deprotonate the terminal alkyne with sodium amide, then use the resulting nucleophile for nucleophilic acyl substitution on an appropriate acyl halide, after which it is reduced using something like sodium borohydride.

sjb:
Is addition to an acyl halide then reduction necessary? Can you use something that corresponds to the reduced acyl halide first?

Meter:

--- Quote from: sjb on March 26, 2021, 02:28:45 AM ---Is addition to an acyl halide then reduction necessary? Can you use something that corresponds to the reduced acyl halide first?

--- End quote ---
Just the equivalent alcohol?

Babcock_Hall:
An alcohol does not have a good leaving group.

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